EP0535627A1 - Unverdauliches Dextrin - Google Patents

Unverdauliches Dextrin Download PDF

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Publication number
EP0535627A1
EP0535627A1 EP92116722A EP92116722A EP0535627A1 EP 0535627 A1 EP0535627 A1 EP 0535627A1 EP 92116722 A EP92116722 A EP 92116722A EP 92116722 A EP92116722 A EP 92116722A EP 0535627 A1 EP0535627 A1 EP 0535627A1
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Prior art keywords
glucose
fraction
dextrin
dietary fiber
kcal
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French (fr)
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EP0535627B1 (de
Inventor
Kazuhiro Ohkuma
Yoshio Hanno
Kazuyuki Inada
Isao Matsuda
Yasuo Katta
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Matsutani Chemical Industries Co Ltd
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Matsutani Chemical Industries Co Ltd
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Priority claimed from JP3336314A external-priority patent/JPH05148301A/ja
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A23G4/10—Chewing gum characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C11/00—Milk substitutes, e.g. coffee whitener compositions
    • A23C11/02—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins
    • A23C11/10—Milk substitutes, e.g. coffee whitener compositions containing at least one non-milk component as source of fats or proteins containing or not lactose but no other milk components as source of fats, carbohydrates or proteins
    • A—HUMAN NECESSITIES
    • A21—BAKING; EDIBLE DOUGHS
    • A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
    • A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
    • A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
    • A21D2/14—Organic oxygen compounds
    • A21D2/18—Carbohydrates
    • A21D2/186—Starches; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00—Milk preparations; Milk powder or milk powder preparations
    • A23C9/12—Fermented milk preparations; Treatment using microorganisms or enzymes
    • A23C9/13—Fermented milk preparations; Treatment using microorganisms or enzymes using additives
    • A23C9/137—Thickening substances
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • A23F3/163—Liquid or semi-liquid tea extract preparations, e.g. gels, liquid extracts in solid capsules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34—Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/346—Finished or semi-finished products in the form of powders, paste or liquids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00—Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/52—Liquid products; Solid products in the form of powders, flakes or granules for making liquid products ; Finished or semi-finished solid products, frozen granules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/163—Sugars; Polysaccharides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/40—Meat products; Meat meal; Preparation or treatment thereof containing additives
    • A23L13/42—Additives other than enzymes or microorganisms in meat products or meat meals
    • A23L13/426—Addition of proteins, carbohydrates or fibrous material from vegetable origin other than sugars or sugar alcohols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L15/00—Egg products; Preparation or treatment thereof
    • A23L15/20—Addition of proteins, e.g. hydrolysates, fats, carbohydrates, natural plant hydrocolloids; Addition of animal or vegetable substances containing proteins, fats, or carbohydrates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/10—Fish meal or powder; Granules, agglomerates or flakes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L25/00—Food consisting mainly of nutmeat or seeds; Preparation or treatment thereof
    • A23L25/10—Peanut butter
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • A23L29/35—Degradation products of starch, e.g. hydrolysates, dextrins; Enzymatically modified starches
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
    • C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
    • C08B30/18—Dextrin, e.g. yellow canari, white dextrin, amylodextrin or maltodextrin; Methods of depolymerisation, e.g. by irradiation or mechanically
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/20—Preparation of compounds containing saccharide radicals produced by the action of an exo-1,4 alpha-glucosidase, e.g. dextrose
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G2200/00—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents
    • A23G2200/06—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF containing organic compounds, e.g. synthetic flavouring agents containing beet sugar or cane sugar if specifically mentioned or containing other carbohydrates, e.g. starches, gums, alcohol sugar, polysaccharides, dextrin or containing high or low amount of carbohydrate

Definitions

  • the present invention relates to indigestible dextrins which are prepared by heat-treating corn starch with addition of an acid and hydrolyzing the resulting starch with alpha-amylase and glucoamylase and which contain dietary fiber and have a low caloric value.
  • Pyrodextrins are prepared by heating a starch containing several percent of water in the presence or absence of acid. These dextrins include British gum which is obtained by heating the starch at 135 to 218°C in the absence of acid for 10 to 20 hours, white dextrin which is prepared by heating the starch at 79 to 121°C in the presence of acid for 3 to 8 hours, and yellow dextrin which is prepared similarly by heating the starch at 150 to 220°C with addition of acid for 6 to 18 hours.
  • pyrodextrin obtained by heat-treating commercial corn starch with addition of hydrochloric acid reveals that the pyrodextrin comprises at least 57.3% of 1 ⁇ 4 glycosidic linkage fraction (2,3,6-Tri-O-Methyl-D-glucose), 2.6% of 1 ⁇ 6 glycosidic linkage fraction (2,3,4-Tri-O-Methyl-D-glucose), up to 1.2% of 1 ⁇ 3 glycosidic linkage fraction (2,4,6-Tri-O-Methyl-D-glucose), 6.3% of a fraction having both 1 ⁇ 4 and 1 ⁇ 6 linkages (2,3-Di-O-Methyl-D-glucose) and about 20% of a fraction having other glycosidic linkages.
  • the analyzed values when calculated for corn starch, correspond to 67% of 1 ⁇ 4 glycosidic linkage fraction (2,3,6-Tri-O-Methyl-D-glucose), 2.7% of 1 ⁇ 3 glycosidic linkage fraction (2,4,6-Tri-O-Methyl-D-glucose) and 7.8% of a fraction having both 1 ⁇ 4 and 1 ⁇ 6 glycosidic linkages (2,3 Di-O-Methyl-D-glucose).
  • any of commercial pyrodextrins was found to be up to 30% in indigestible content, up to 3% in dietary fiber content, at least 3.1 kcal/g in caloric value 1 and at least 3.1 kcal/g in caloric value 2.
  • starch was heated under altered conditions to increase these contents, it was possible to increase the indigestible content to about 60% and the dietary fiber content to about 30% and to decrease the caloric value 1 to about 2.7 kcal/g and the caloric value 2 to about 2 kcal/g, whereas the product then contained an increased amount of colored substance, had a stimulative odor, therefore required refining and was not practically useful because of extreme difficulties encountered in refining the product.
  • a dextrin which is at least 75% in indigestible content, at least 20% in dietary fiber content, up to 2.6 kcal/g in caloric value 1 and up to 2 kcal/g in caloric value 2 as contemplated by the present invention.
  • U.S. Patent No. 3,974,032 discloses a hydrolyzate which is prepared from a pyrodextrin obtained with addition of hydrochloric acid and having a degree of branching of 7 to 16% by hydrolyzing the pyrodextrin at 60 to 85°C to DE of 9 to 20 with alpha-amylase and which is up to 20 in the ratio of weight average molecular weight to number average molecular weight and contains up to 20% of oligosaccharides having a degree of polymerization of 200.
  • the patent discloses nothing about hydrolysis with glucoamylase or about dietary fiber.
  • Indigestible substances such as dietary fibers and oligosaccharides, exhibit various modes of behavior in the digestive tracts producing physiological effects on the living body.
  • First in the upper digestive tract water-soluble dietary fibers slow the transport of food and delay the absorption of nutrients. Delayed absorption of sugar, for example, suppresses the rise in blood sugar value, consequently lowering insulin requirements. Further, excretion of bile acid is promoted, diminishing the sterol group in the body lowering the cholesterol level of the serum.
  • Other physiological effects through the endocrine system of the body are also reported.
  • indigestible substances are not digested or absorbed by the digestive tract, including the small intestine and reach the large intestine.
  • oligosaccharides and dietary fibers are partly acted on by enterobacteria yielding short-chain fatty acids, intestinal gases, vitamins, etc. Acidification of the intestinal environment by the short-chain fatty acids condition the intestine.
  • dietary fiber hypothesis suggested by Trowell and Burkitt epidemiologically revealed that there is a negative correlation between the intake of dietary fibers and the onset of non-infectious diseases such as cholelithiasis, ischemic heart diseases, cancer of the large intestine, etc.
  • non-infectious diseases such as cholelithiasis, ischemic heart diseases, cancer of the large intestine, etc.
  • insufficient ingestion of dietary fibers is thought to be a cause of degenerative diseases which are said to be diseases of the Western type.
  • the dietary fibers are defined as the "whole group of indigestible components of foods which are not digestible by human digestive enzymes" and are classified into insoluble dietary fibers and water-soluble dietary fibers according to the solubility in water. Of these, water-soluble dietary fibers have attracted attention as materials for functional foods and livestock feeds because of their great physiological function.
  • water-soluble dietary fibers examples include guar gum, glucomannan, pectin and like natural gums which have high viscosity which are difficult to ingest singly in a large amount. Further the addition of these fibers to processed foods encounters problems in preparing the food and presents difficulties with respect to texture. It has therefore long been desired to provide dietary fibers of low viscosity which have the same physiological functions as the above fibers, are easy to ingest and are user-friendly in preparing processed foods.
  • low caloric sweeteners include various indigestible oligosaccharides and sugar alcohols, which nevertheless have many problems with respect to the quality, degree of sweetness, oligosaccharide content and likelihood of causing laxation.
  • the bulking agent available for use with strong sweetening agents such as aspartame is polydextrose only, whereas polydextrose is ingestible in a limited amount, tastes bitter in an acid condition, is hygroscopic and therefore has problems.
  • starch is used in large quantities in various processed foods as a food material.
  • Useful food materials of these types include starch and starch products such as pregelatinized starch, pyrodextrin, derivatives, glucose, corn syrup solids and maltodextrin.
  • starch and starch products such as pregelatinized starch, pyrodextrin, derivatives, glucose, corn syrup solids and maltodextrin.
  • a majority of these starch products are not higher than 5% in the content of indigestible component and at least 3.9 kcal/ g in caloric value, so that among starches and like materials, only pyrodextrin appears useful as a dietary fiber and low caloric material.
  • Heat-treated starch pyrodextrin
  • dextrin Heat-treated starch
  • the main object of the present invention is to provide a novel indigestible dextrin which is diminished in the amount of colored substance and stimulative odor and which contains at least 75% of an indigestible component and at least 13% of dietary fiber and is up to 2.6 kcal/g in caloric value 1 and up to 2 kcal/g in caloric value 2.
  • the portion of the dextrin other than glucose contains at least 90% of an indigestible component and at least 20% of dietary fiber and is up to 1.8 kcal/g in caloric value 1 and up to 1.2 kcal/g in caloric value 2.
  • the foregoing object of the present invention can be fulfilled by determining the structural requirement of the pyrodextrin to be used as the starting material of the invention and by providing an indigestible dextrin by hydrolyzing the pyrodextrin with alpha-amylase and glucoamylase and separating off a digestible fraction from the resulting hydrolyzate by ion exchange resin chromato-graphy.
  • the values of analytical data as to samples (especially those of dextrin for use in the present invention) herein given are those calculated as solids.
  • the number average molecular weight will be abbreviated as MN, the weight average molecular weight as MW, and the ratio of weight average molecular weight to number average molecular weight as MW/MN.
  • Glucose residues having a 1 ⁇ 4 linkage only will be expressed as "glucose residues having a 1 ⁇ 4 linkage,” and similar expressions will be used also for 1 ⁇ 6 linkage and 1 ⁇ 3 linkage.
  • the numerical values used for the compositions of food examples and feed examples are those of moisture-containing components.
  • the dietary fiber contents and caloric values given in these examples, except for those of indigestible dextrin, are calculated according to "Tables of Standard Compositions of Japanese Foods," Fourth Edition (edited by Science & Technology Agency, Resources Council, 1982).
  • the starch to be used for preparing the indigestible dextrin of the invention is corn starch, to which an acid needs to be used as a catalyst.
  • various acids are usable, hydrochloric acid is especially preferable to use since the product is used for foods.
  • the product preferable has higher contents of indigestible component and dietary fiber.
  • the product should contain at least 75% of an indigestible component and at least 13% of dietary fiber and should be up to 2.6 kcal/g in caloric value 1 and up to 2 kcal/g in caloric value 2.
  • the fraction of the product other than glucose should contain at least 90% of an indigestible component and at least 20% of dietary fiber and should be up to 1.8 kcal/g in caloric value 1 and up to 1.2 kcal/g in caloric value 2.
  • pyrodextrins include white dextrin which has heretofore been used generally for foods and pharmaceuticals.
  • White dextrin contains up to 30% of indigestible component and up to 3% of dietary fiber, is about 3.9 kcal/g in both caloric values 1 and 2, and is therefore unusable for foods. Further when containing at least 30% of indigestible component and at least 12% of dietary fiber and having caloric values 1 and 2 of up to 3 kcal/g, such dextrin tastes stimulating and can not be used therefore.
  • the pyrodextrin for use in the present invention is prepared by adding an aqueous solution of hydrochloric acid, about 1% in concentration, to starch in an amount of 3 to 10% based on the starch, and heating the starch. Since the aqueous acid solution is added before the heat treatment, the starch and the acid are uniformly mixed together by being agitated and aged in a mixer, and the mixture is then heated at 150 to 200°C for 10 to 120 minutes, preferably for 15 to 60 minutes, unlike the heating condition for preparing conventional pyrodextrins (white dextrin and yellow dextrin).
  • reaction temperature is higher, the resulting product will contain increased amount of indigestible component and dietary fiber and have a lower caloric value, whereas increased amount of colored substance will be formed as the temperature rises from about 180°C, so that the temperature is preferably 150 to 180°C.
  • the reaction can be conducted at a high temperature within a shortened period of time by suitably selecting the heater to be used, the mixture can be heat-treated efficiently using an apparatus capable of effecting a uniform reaction. Further because the starch is reacted in the form of powder, there arises a need to alter the heating condition for mass production, so that it is desirable to suitably vary the heating condition by checking the quality of the product as treated.
  • alpha-amylases are those commercially available, among which TERMAMYL (heat-resistant alpha-amylase produced by Bacillus licheniformis and manufactured by NOVO Industry Co., Ltd.) is most desirable.
  • the solution Since the pyrodextrin solution has been made acidic with the acid added before the heat treatment, the solution must be adjusted to an optimum pH value for the amylase to be used, with any of common alkalis.
  • Sodium hydroxide is commercially available in the form of a solution and is therefore most advantageous to use.
  • the preferred pH is 5.5 to 6.5. If the value is lower than this range, a reduced reaction velocity will result, whereas higher pH values entail pronounced coloration.
  • alpha-amylase is added to the solution usually in an amount of about 0.05 to about 0.2%.
  • the reaction temperature need not to be as high as that is used for the preparation of maltodextrin. Since high temperature rather results in promoted coloration, the temperature is preferably 80 to 90°C. Satisfactory results can be achieved by conducting the reaction usually for about 1 hour.
  • the reaction mixture is subsequently hydrolyzed with glucoamylase.
  • Any of commercial glucoamylase is useful for this purpose.
  • Glucoamylase generally contains a small amount of alpha-amylase, so that glucoamylase, if singly used, exhibits the effect to be produced by the conjoint use of alpha-amylase and glucoamylase. However, when the amount of alpha-amylase contained is lesser, the effect achieved is slightly smaller than is contemplated by the invention. The most preferred result can be achieved by using alpha-amylase and glucoamylase in combination.
  • the pH preferable for the activity of glucoamylase is 4.0 to 6.0. Like alpha-amylase, glucoamylase is used in an amount of about 0.05 to about 0.2%.
  • the reaction is conducted at a temperature of about 55 to about 60°C usually for 24 to 48 hours.
  • the amount of each of the amylases to be used is not limited to the foregoing range but may be used in an amount equivalent thereto in accordance with the activity of the amylase.
  • the reaction time is controllable as desired by varying the amount.
  • the hydrolyzate obtained by hydrolyzing pyrodextrin with alpha-amylase may be autoclaved at 115 to 135°C, then reacted with alpha-amylase again and thereafter with glucoamylase, whereby the hydrolyzate can be filtered at a higher rate for refining.
  • the hydrolyzate resulting from the reaction with glucoamylase is lowered in pH to about 3.5, then heated to about 80°C, and thereafter decolorized with activated carbon, filtered, and desalted and decolorized with ion exchange resin in usual manner.
  • the hydrolyzate is subsequently concentrated to a concentration of about 50% and thereafter subjected to continuous ion exchange resin chromatography to separate off the glucose formed.
  • commercial strongly acidic cation exchange resins are usable.
  • Examples of such resins which are desirable are AMBERLITE IR-116,IR-118, IR120-B, XT-1022E and XT-471F (brand names for products of Japan Organo Co., Ltd.), DIAION 2K-1B, SKK-102, SK-104, SK-106,SK-110, SK-112, SK-116 and FR-01 (brand names for products of Mitsubishi Chemical Industries, Ltd.), and XFS-43281.00, -43280.00, -43279.00 and -43278.00 (brand names for products of Dow Chemical Japan).
  • the hydrolyzate is passed through the column at a temperature of 20 to 70°C, preferably 50 to 70°C. At lower temperature, inefficient separation will result, and an increase in the viscosity of the liquid is likely to cause trouble to the resin, whereas at higher temperature exceeding the specified range, the liquid is likely to turn brown or become otherwise degraded.
  • the separation procedure decreases the glucose content to about 0.5%
  • the glucose content is adjustable as desired by altering the separation condition. Accordingly, in the case where it is desired to use the glucose as a sweetener, the product can be obtained with an increased glucose content.
  • the hydrolyzate as treated with glucoamylase has a glucose content of 50%
  • a product with an overall glucose content of about 33% can be obtained by separating off one-half, i.e., 25%, of the glucose from the hydrolyzate.
  • the content was measured by a modified method according to "The method for determining the indigestible part using HPLC” (Journal of Japanese Society of Starch Science, Vol. 37, No. 2, p. 107, 1990) as will be described below.
  • a sample was methylated by a modified method of Hakomori's methylation method (S. Hakomori, J. Biochem., 55, 205(1964)) described below, followed by hydrolysis and thereafter by gas chromatography to quantitatively determine the glycosidic linkages composing the sample.
  • a dehydrated sample (100 to 200 ⁇ g ) is placed into a test tube (15 mm diam. ⁇ 100 mm ) with a screw cap and dissolved by addition of 0.3 ml of DMSO.
  • To the solution is added 20 mg of NaH, immediately followed by addition of 0.1 ml of methyl iodide.
  • the mixture is stirred by a touch mixer for 6 minutes and then cooled in ice water, and 2 ml of water is added to the mixture.
  • the mixture is fully shaken with addition of 2 ml of chloroform.
  • the upper layer (aqueous layer) is collected with a pipette and discarded.
  • the remaining layer is similarly washed with addition of 2 ml of water. This procedure is repeated 6 times.
  • Cotton is placed on the bottom of a Pasteur pipette, anhydrous sodium sulfate is placed into the pipette to form a 4- to 5- cm -thick layer, and the solution is passed through the layer for dehydration and then washed with chloroform. Subsequently, the solution is concentrated to dryness in a rotary evaporator.
  • the methylated product is hydrolyzed at 100°C for 4 hours, and the hydrolyzate is concentrated to dryness at 60°C in a rotary evaporator.
  • the hydrolyzate is dissolved in 0.5 ml of water, and the solution is allowed to stand at room temperature for 2 hours with addition of 10 mg of sodium borohydride. Several drops of acetic acid are added to the mixture until the mixture ceases forming to terminate the reaction. The mixture is then dried at room temperature and further dried at room temperature with addition of 1 ml of methanol to remove the boric acid formed. This procedure is repeated 6 times.
  • the reduced product With addition of 0.5 ml of acetic anhydride, the reduced product is heated at 100°C for 4 hours and thereby acetylated. With addition of 1 ml of toluene, the product is concentrated to dryness in a rotary evaporator.
  • the acetylated product is dissolved in 1 ml of chloroform, the solution is shaken with addition of 1 ml of water, and the aqueous layer is discarded. After repeating this procedure 5 times, the chloroform is evaporated off from the resulting layer by a rotary evaporator.
  • the desalted product is dissolved in 0.5 ml of chloroform and subjected to gas chromatography.
  • the same solution as used for the quantitative determination of glucose is passed through a column of ion exchange resin of the mixed bed type at SV of 1.0 for desalting, and the effluent is concentrated to a concentration of 5% using a rotary evaporator to obtain a sample.
  • a 20- ⁇ l protion of the sample is subjected to liquid chromatography under the following conditions.
  • the effective caloric value of a sample is calculated as the sum of the caloric value resulting from digestion and absorption by the digestive system up to the upper digestive tract, and the caloric value resulting from intestinal fermentation after arrival of the sample at the large intestine.
  • Test 1 Measurement of caloric value resulting from digestion and absorption by the upper digestive tract up to the small intestine
  • the sample is dissolved in 45mM (bis)Tris buffer (pH 6.0) containing 0.9mM calcium chloride to obtain a 4.55% solution, to which 160 U/ g of human saliva alpha-amylase (SIGMA Type IX-A) is added, followed by a reaction at 37°C for 30 minutes. After deactivating the enzyme, the reaction mixture is desalted with an ion exchange resin and adjusted to a concentration of 1.1%. The aqueous solution (4 ml ) is then added to 2 ml of 50mM hydrochloric acid-potassium chloride buffer (pH 2.0), and the mixture is maintained at 37°C for 100 minutes, followed by desalting with an ion exchange resin.
  • the powdery sample thus obtained is dissolved in 45mM sodium maleate buffer (pH 6.6) to prepare a 0.45% solution, with which 86U/ g of rat small intestine mucous membrane enzyme (product of SIGMA) is reacted at 37°C for 3 hours.
  • the amount of glucose produced is measured by the pyranose oxidase method.
  • the caloric value to be produced by digestion and absorption is calculated from the following equation.
  • Test 2 Determination of caloric value resulting from intestinal fermentation
  • the caloric value of the fraction reaching the large intestine was determined by the growth curve method using rats as described below.
  • Table 1 Component Proportion(%) Corn starch 42.7 Casein 40.0 Fiber 2.0 Mineral mixture 10.0 Vitamin mixture 0.8 DL-methionine 0.3 Choline bitartrate 0.2 Vegetable oil 5.0
  • Rats were preliminarily raised for 5 days to adapt them to the laboratory environment and to the basal diet shown in Table 1, then checked for body weight and health and divided into groups (10 rats in each group).
  • the average initial body weight of all the test groups was 79.6 to 80.8 g .
  • the body weight variations of the groups were in the range of 9 to 16 g .
  • the caloric value of all the test components and basal diet was measured by a bomb calorimeter. Table 2 No.
  • the rats were placed into individual steel cages and fed according to the experimental schedule listed in Table 2.
  • the basal diet was given to all the rats in an amount of 5.4 g /rat/ kg (22.7 kcal/rat/day).
  • glucose or the above sample was added in an amount of 0.5, 1.0, 2.0 or 4.0 g to the basal diet.
  • the amount of glucose or sample added was about 2, 4, 8 or 16 kcal/rat/day in terms of caloric value.
  • the amount of ingestion was measured daily, and the gain in the body weight was measured on the 0th, 5th, 10th and 15th days.
  • the rats were checked generally every day by observation. Table 3 shows the results. Table 3 No.
  • the caloric value was calculated from the following equation.
  • Detected by this procedure were a glucose residue at each nonreducing end, glucose residues having a 1 ⁇ 4 linkage, glucose residues having a 1 ⁇ 6 linkage, glucose residues having a 1 ⁇ 3 linkage, glucose residues each having both 1 ⁇ 4 linkage and 1 ⁇ 6 linkage, glucose residues each having both 1 ⁇ 3 linkage and 1 ⁇ 4 linkage, glucose residues each having both 1 ⁇ 2 linkage and 1 ⁇ 4 linkage, and glucose residues having other linkages.
  • the value of glucose determined by the method used included the content of glucose residues at the nonreducing ends, so that the content of glucose residues given is this value minus the content of glucose. Table 4 shows the values obtained.
  • the method of quantitative determination is complex and involves errors which are usually about ⁇ 5% and are invariably ⁇ 2% if minimum.
  • the contents of indigestible component and dietary fiber increase in proportion to the heating time.
  • the caloric values decrease in inverse proportion to the heating time.
  • the contents of glucose residues with various glycosidic linkages i.e., those having 1 ⁇ 6 glycosidic linkage, those having 1 ⁇ 3 glycosidic linkage, those having both 1 ⁇ 4 and 1 ⁇ 6 glycosidic linkages, those having both 1 ⁇ 2 and 1 ⁇ 4 glycosidic linkages, and those having other linkages, increase in proportion to the heating time.
  • Only the content of residues with 1 ⁇ 4 linkage decreases in inverse proportion to the heating time.
  • the values MN and MW/MN decrease during heating for 15 minutes and increase again in proportion to the heating time after 30 minutes.
  • Table 5 reveals the following distinct features.
  • Table 6 reveals that the hydrolyzates before being hydrolyzed with glucoamylase were as high as about 36 to about 280 in MW/MN.
  • the content (%) of indigestible component in the fraction other than glucose is a value obtained by subtracting the glucose content (%) from 100, dividing the measured amount of indigestible component by the remainder and multiplying the quotient by 100.
  • the content (%) of dietary fiber in the fraction other than glucose is a value obtained by subtracting the glucose content (%) from 100, dividing the measured amount of dietary fiber by the remainder and multiplying the quotient by 100.
  • the caloric value of the fraction other than glucose is a value obtained by multiplying the glucose content (%) by 4 (caloric value of 1 g of glucose), dividing the product by 100 and subtracting the quotient from the measured caloric value.
  • the theoretical yield is a value obtained by subtracting the glucose content of Table 5 from 100.
  • the content of indigestible component and the caloric values each remain substantially unchanged with the heating time, but the dietary fiber content increases in proportion to the heating time.
  • the theoretical yield which corresponds to the proportions of indigestible component, dietary fiber and low calorie component, increases in proportion to MN, MW and MW/MN.
  • the table further reveals that the theoretical yield increases to at least about 65% when MW/MN is at least 25. This indicates that the hydrolyzate before the separation of the glucose fraction by the ion exchange resin is high in the contents of indigestible component and dietary fiber and low in caloric values.
  • the content of indigestible component in the overall hydrolyzate containing glucose can be readily obtained by subtracting the glucose content (%) from 100, multiplying the corresponding content of Table 7 by the remainder and dividing the product by 100.
  • the content of dietary fiber in the overall hydrolyzate containing glucose can be obtained by subtracting the glucose content (%) from 100, multiplying the corresponding content of Table 7 by the remainder and dividing the product by 100.
  • the caloric value of the overall hydrolyzate containing glucose can be obtained by multiplying the glucose content (%) by 4, dividing the product by 100 and adding the quotient to the caloric value of Table 7.)
  • the relationship between the important value MN and the different glycosidic linkage fractions was investigated by regression analysis for determining the correlation between variables to obtain equations and correlation coefficients.
  • the correlation analysis was conducted for the five samples except the sample which was obtained by 180 minutes heating and wherein the component sugars appeared to have been broken down, using the amounts of glucose residues having various glycosidic linkages as predictor variables and the MN values as criterion variables.
  • Equation 1 reveals the novel fact that the smaller the amount of glucose residue having a 1 ⁇ 4 glycosidic linkage, the greater the MN, that is, the higher the content of indigestible component and dietary fiber the lower the caloric value.
  • the sample of Experimental Example 2 obtained by 30 minutes heating was concentrated to prepare about 1.5 liters of 50% solution.
  • the solution (100 ml ) was passed through a column packed with 160 ml of Ionpack S-2006 (product of Showa Denko Co., Ltd.) which is a styrene-divinylbenzene copolymer of the sodium type having its molecular weight corrected with pullulan, at a column temperature of 60°C and at SV of 0.25.
  • water was passed through the column to collect four fractions (as separated from a fraction of glucose and oligosaccharides). The four fractions were checked for the content of dietary fiber.
  • Table 10 shows the result.
  • Table 10 Sample No. 1 2 3 4 content of dietary fiber (%) 90.3 51.5 44.2 23.4
  • the dietary fiber content which was 37.4% in Table 7, increased to a maximum of 90.3% as shown in Table 10.
  • a sample was prepared in the same manner as in Experimental Example 4 with the exception of adding 22.5 liters of 1% hydrochloric acid to 300 kg of commercial tapioca starch, treating the mixture in the same manner as in Experimental Example 1 and heating the mixture at 165°C for 1 hour.
  • the sample was analyzed in the same manner as in Experimental Example 4, and MN was calculated from Equation 1.
  • Table 11 shows the results obtained in Comparative Examples 1 and 2.
  • Table 11 Item Comp. Ex. 1 2 Contents of linkage (%) non-reduced end 28.6 23.9 1 ⁇ 4 30.0 25.0 1 ⁇ 6 11.7 13.9 1 ⁇ 3 9.6 10.8 1 ⁇ 4, 1 ⁇ 6 10.4 9.5 1 ⁇ 3, 1 ⁇ 4 1.8 1.5 1 ⁇ 2, 1 ⁇ 4 2.7 2.9 others 5.2 12.5 content of glucose (%) 1.2 1.2 content of indigestible component (%) 97.3 94.3 content of dietary fiber(%) 25.1 33.9 caloric value 1(kcal/ g ) 1.68 1.75 caloric value 2(kcal/ g ) 1.08 1.17 MN measured value 750 1119 MN culculated value 928 1363 Difference between calculated value and measurement (%) +23.7 +21.9
  • the eight pyrodextrin samples obtained in Experimental Examples 1, 4 and 5 were checked for the degree of coloration by measuring the whiteness of the samples relative to the whiteness of magnesium oxide taken as 100%, using photoelectric whiteness meter (product of Kett Co.) and a blue filter. Table 12 shows the results. Table 12 Ex. heating temp. (°C) heating time (min.) Whiteness (%) 1 165 10 72.3 1 165 15 68.2 1 165 30 47.9 1 165 60 38.5 1 165 120 33.8 1 165 180 30.8 4 180 30 46.8 5 150 60 49.4
  • Table 12 shows that the whiteness decreases in inverse proportion to the heating time and heating temperature.
  • Examples A and B were used, which will be referred to as "samples A and B," respectively, in Experimental Examples 7 to 11.
  • the sample A was given at a daily dose of 10 g to ten males in good health during a test period of 2 weeks. During the first and second weeks of the test period, they are given the same meals in same quantities, and the sample was administered after breakfast on Monday through Friday. Feces were collected on every defecation and checked for wet weight, dry weight, moisture content and frequency of defecation. Table 13 shows the results, which reveal that the sample has an effect to increase the overall amount of feces.
  • Each value listed is mean value ⁇ standard deviation, and the mark * indicates a significance level of 5% relative to the non-ingestion period, hence a significant difference.
  • the sample B was checked for a constipation alleviating effect.
  • the sample was given to 25 volunteers having a tendency toward constipation at a predetermined dose for at least 5 days. Changes resulting from the administration of the sample in defecation were checked with a questionnaire. Scores were assigned to the check items on the questionnaire according to the following criteria to substantiate the effect through a statistical procedure.
  • the sample B when administered at a dose of at least 5 g , resulted in increased scores and was found effective for alleviating constipation.
  • mice of Sprague-Dawley strain (6 rats/group) initially weighing about 50 g were accommodated in individual cages placed in a small animal breeding chanber controlled to 23 ⁇ 2°C, preliminarily raised with a commercial synthetic diet for 1 week, and thereafter fed for 7 days with a basal diet shown in Table 15, or the basal diet containing 5% of the sample A added thereto, or the basal diet containing 5% of cellulose ( Avicel, product of Sanyo-Kokusaku Pulp Co., Ltd.) with free access to water and the diet. The intake of diet and change in body weight were recorded daily.
  • Rats were used for a nutritional experiment to check the samples A and B for a serum lipid lowering effect.
  • basal diet basal diet
  • test diet comprising 95 % of the basal diet and 5 % of the sample A or B admixed therewith was given to the second group (sample A group) and the third group (sample B group), with free access to the diet and water.
  • the results achieved by the test groups are expressed in mean values.
  • the sample A (10 g ) was dissolved in 100 ml of water, and the solution was orally given to 10 persons three times a day before every meal for two months, during which they observed usual eating habit and were allowed to perform routine work.
  • the persons participating in the test were 33 to 59 years old (50.3 in average age), 158 to 173 cm tall (164.8 cm on the average) and weighed 52 to 82 kg (68.8 kg on the average).
  • FIG. 1 and FIG. 2 shows the results obtained.
  • FIG. 1 and FIG 2 reveal that the administration of the sample A altered the serum total cholesterol value toward the normal value (120-250 mg / dl ). Those who were higher than the normal in this value exhibited a reduction, while those who were lower than the normal exhibited a value in the normal range. A similar result was observed also with respect to the neutral fat value. These results substantiate that the sample A has a remarkable effect improving serum lipid metabolism.
  • the product of the invention obtained by hydrolyzing pyrodextrin with alpha-amylase and glucoamylase distinctly differs from known pyrodextrins with respect to the following. More specifically stated, the fraction of the present dextrin other than glucose has the following features.
  • the product of the invention is a novel substance containing exceedingly larger amounts of indigestible component and dietary fiber and having a lower caloric value than conventional pyrodextrins, and greatly different from known pyrodextrins in structure.
  • the Experimental data further indicates that the whiteness decreases in inverse proportion to the heating time.
  • the decrease in whiteness demonstrates an increase in the amount of colored substance due to the heat treatment.
  • the increase in the amount of colored substance presents difficulty in refining the product before the separation, consequently lowering the efficiency of the ion exchange resin for use in the separation treatment.
  • the whiteness must therefore be at least 30%, preferably at least 40%.
  • Table 12 shows that the heat treatment is to be conducted preferably for not more than 60 minutes when the heating temperature is 150°C, or for not longer than about 45 minutes at 165°C or for not longer than 30 minutes at 180°C.
  • the progress of the reaction can be controlled by varying the amount of acid to be added to corn starch, use of a greatly increased amount of acid causes corrosion or abrasion to the apparatus, so that the optimum amount of acid to be used is up to 3000ppm, preferably about 1000ppm, based on the starch.
  • glucoamylase product of Daiwa Kasei Co., Ltd.
  • the resulting hydrolyzate was adjusted to a pH of 3.6 to inactivate the glucoamylaze.
  • the hydrolyzate was decolorized with activated carbon, filtered, desalted with ion exchange resins and thereafter concentrated to obtain a 50% solution.
  • a 20 liter portion of the solution was passed at 60°C at SV 0.25 through the column of a continuous chromatographic device packed with 10 liters of XFS-43279.00 (product of Dow Chemical Japan), which is a strongly acidic cation exchange resin of the sodium type.
  • water was passed through the column to separate off a glucose fraction and obtain an indigestible fraction.
  • the fraction was concentrated to obtain about 5 kg of an indigestible dextrin having a moisture content of 4.4%.
  • the resulting hydrolyzate was cooled to a temperature of 55°C, adjusted to a pH of 5.5 and hydrolyzed for 36 hours with 0.2 wt. % of glucoamylase (product of Daiwa Kasei Co., Ltd.) added thereto, whereupon the hydrolyzate was adjusted to a pH of 3.5 to inactivate the glucoamylaze.
  • the hydrolyzate was refined in the same manner as in Example 1 and further treated in the same manner as in Example 1 with the exception of using potassium-type AMBERLITE IR-118 (product of Japan Organo Co., Ltd.) as a strongly acidic ion exchange resin, whereby an indigestible fraction was obtained. This fraction was concentrated to a concentration of 50% and then spray-dried, affording about 4.5 kg of an indigestible dextrin having a moisture content of 4.2%
  • the resulting hydrolyzate was adjusted to a pH of 3.5 to inactivate the glucoamylase.
  • the hydrolyzate was thereafter treated in the same manner as in Example 2, giving about 4 kg of an indigestible dextrin having a moisture content of 4.8%.
  • the hydrolyzate was then autoclaved at 125°C for 10 minutes, thereafter discharged into the atmosphere, cooled to a temperature of 57°C, adjusted to a pH 5.5 and hydrolyzed for 36 hours with 0.1 wt.% of glucoamylase (product of Daiwa Kasei Co., Ltd.) added thereto.
  • the resulting hydrolyzate was adjusted to a pH of 3.6 to inactivate the glucoamylase.
  • the hydrolyzate was refined and concentrated in the same manner as in Example 1 to obtain a 52% solution.
  • a 20 liter portion of the solution was passed at 60°C at SV 0.3 through the column of a continuous chromatographic device packed with 10 liters of DIAION SKK-116 (product of Mitsubishi Chemical Industries, Ltd.), which is a strongly acidic cation exchange resin of the sodium type. Subsequently, water was passed through the column to separate off 52% of glucose formed and obtain an indigestible fraction. The fraction was concentrated to obtain about 8 kg of a liquid indigestible dextrin having a concentration of 70%.
  • the appearent glucose separation persentages in these four examples are 97.5%, 87.8% 79.3% and 51.1%, respectively.
  • the indigestible dextrin of the present invention is usable for almost all foods.
  • the term "foods” as used herein refers collectively to foods for man and feeds for livestock and for use in zoos and for pets.
  • the indigestible dextrin is prepared from starch, is soluble in water, contains dietary fiber, and is usable also as a low calorie bulking agent in foods, so that it is usable in any food wherein dextrin and maltodextrin are usually usable.
  • the indigestible dextrin is effectively usable for liquid or powdery beverages such as coffee, black tea, cola and juice; baked products such as bread, cookies, crackers, cakes, pizza and pies; noodles such as wheat noodles, Chinese noodles and buckwheat noodles; pasta such as spaghetti, macaroni and fettuccine; confectionery such as candies, chocolate and chewing gum; doughnut, potato chips and like fried cakes or foods; ices such as ice cream, shakes and sherbets; daily products such as cream, cheese, milk powder, condensed milk, creamy powder, coffee whitener and milk beverages; chilled desserts such as custard pudding, yoghurt, drinkable yoghurt, jelly, mousse and Bavarian; retorted pouched or canned foods such as soups, stew, gratin and curries; seasonings such as bean paste, soy sauce, Worceter sauce, ketchup, mayonnaise, dressing, bouillon and roux; processed meat products such as ham, sausage, hamburger, meat
  • the dextrin is difficult to use in emulsified foods of the W/O type, such as margarin, since the dextrin incorporated therein is liable to separate off during preservation.
  • the dextrin can be added to the food of the inventionin in an amount which is not limited insofar as the quality of the food is not impaired.
  • the amount of the agent to be taken is preferably not greater than half of this value, i.e., up to about 1 g / kg body weight. Nevertheless, since the influence on physiological activities differs from person to person, it is most desirable to alter the amount in view of the effect achieved by the ingestion of the low calorie foods.
  • the indigestible dextrin is about 10 in sweetness, tasting slightly sweet.
  • FIG.1 shows the result along with the corresponding values of sucrose, gum arabic and maltodextrin.
  • FIG.1 stands for the following.
  • the indigestible dextrin is not greatly different in the increase of coloration degree from glucose or maltose. This indicates that the indigestible dextrin is usable generally in the same manner as these materials.
  • FIG.4 shows the result along with the result achieved by maltodextrin.
  • the symbols used in FIG.4 have the same meaning as in FIG.1.
  • the indigestible dextrin is much less than maltodextrin in increases in turbidity and is therefore very suitable for use in frozen foods.
  • FIG.5 shows the result obtained by checking 5 to 30% aqueous solutions of indigestible dextrin for freezing point depression along with the result achieved by sucrose and maltodextrin.
  • the symbols in FIG.5 are the same as in FIG.1.
  • the indigestible dextrin is generally intermediate between sugar and maltodextrin in the degree of freezing point depression and is therefore suited to use in ices and the like.
  • the indigestible dextrin was made anhydrous by drying and then allowed to stand in a constant-humidity container at 20°C and a relative humidity of 81%, 52% or 32% for 200 hours.
  • FIG. 6 shows the hygroscopicity of the indigestible dextrin thus determined.
  • the water content of the indigestible dextrin will not exceed 18% even if preserved for a long period of time.
  • the indigestible dextrin is therefore suited to use in powdery foods.
  • FIGS.7 to 9 show the results.
  • FIG.7 shows a control mix; FIG.8, a sugar mix and FIG.9, an indigestible dextrin mix (low calorie mix containing dietary fiber).
  • Table 20 Control Sugar Example 1 Hard flour ( g ) 35.0 35.0 35.0 Sugar ( g ) - 1.75 - Example 6 ( g ) - - 1.75 Water ( g ) 26.0 25.5 25.5 Ratio of water added (%) 74.3 72.9 72.9 Developping time (min) 4.5 4.0 5.5
  • Black tea of the composition given in Table 21 was prepared.
  • Table 21 Black tea Control Example Black tea extract 97.0 97.0 Sugar 3.0 3.0 Dextrin (Example 3 - 8.0 Dietary fiber 0 2.52 Dietary fiber/240 g 0 5.64
  • Cola of the composition given in Table 22 was prepared.
  • Table 22 Cola drink Control
  • Sugar 11.0 11.0 Cola base 0.3 0.3 Citric acid 0.05 0.05 Soda water 89.65 89.65 Dextrin (Example 1) - 10.0 Dietary fiber 0 3.80 Dietary fiber/240 g 0 8.29
  • Orange juice (30%) was prepared according to the recipe given in Table 23 dissolving powdery ingredients in water, adding condensed juice and flavoring to the solution and homogenizing the mixture by a homomixer.
  • Table 23 Orange juice (30%) Control Example Orange juice concentrate (BX.45) 6.7 6.7 Sugar 8.1 8.1 Citric acid 0.3 0.3 Sodium citrate 0.1 0.1 Orange flavor 0.3 0.3 Water 84.5 84.5 Dextrin (Example 1) - 4.0 Dietary fiber 0.07 1.59 Dietary fiber/240 g 0.17 3.67
  • a sports beverage was prepared by mixing all ingredients with water according to the recipe of Table 24 and sterilizing the mixture by heating.
  • Table 24 Sports drink Control Example Salt 0.5 0.5 Vitamin C 0.03 0.03 Vitamin B1 ⁇ Sodium salt 0.03 0.03 Magnesium chloride 0.2 0.2 Calcium lactate 0.2 0.2 Citric acid 2.4 2.4 Sodium citrate 1.7 1.7 Flavor 2.0 2.0 Dextrose 80.0 80.0 Fructose 12.94 12.94 Water 1500.0 1500.0 Dextrin (Example 1) - 55.0 Total 1600.0 1655.0 Dietary fiber 0 20.9 Dietary fiber/240 g 0 3.03
  • a milk shake was prepared by mixing all ingredients with water, heating the mixture to 80°C for dissolving, homogenizing the milk fat by a homogenizer, aging the mixture overnight at 5°C, then freezing the mixture, thereafter rapidly cooling the mixture to - 40°C and fully shaking the mixture.
  • ice cream was prepared by mixing all ingredients together, heating the mixture to 70°C, stirring the mixture by a homomixer, thereafter homogenizing the mixture by a homogenizer, aging the mixture in a refrigerator for 1 day, freezing the mixture and thereafter rapidly cooling the mixture to -40°C.
  • skim milk as fermented and ground, was mixed with other ingredients, and the mixture was treated by a homogenizer to prepare a yogurt drink.
  • Table 27 Yoghurt (Soft) Control Example Fermented skimmed milk 38.0 38.0 Sugar 13.0 13.0 Stabilizer 0.35 0.35 Flavor 0.05 0.05 Water 48.6 38.6 Dextrin (Example 4) - 10.0 Dietary fiber 0.03 2.03 Dietary fiber/240 g 0.07 4.87
  • hard yogurt was prepared by adding a hardening agent to skim milk, innoculating the mixture with 3% of starter, refrigerating the mixture when acidity of 0.7% was attained, mixing the mixture with other ingredients by stirring and refrigerating the resulting mixture again.
  • Table 28 Yoghurt (Hard) Control Example Skimmed milk 87.0 87.0 Sugar 13.0 - Dextrin (Example 1) - 13.0 Stevioside - 0.05 Flavor Small amt. Small amt. Gelatin Small amt. Small amt. Dietary fiber 0.07 5.01 Dietary fiber/150 g 0.11 7.52 Caloric val.1(KCal/100 g ) 78 49 Caloric val.2(KCal/100 g ) 78 41
  • a powder of coffee whitener was prepared by dissolving water-soluble ingredients in 66.6% of hot water based on the dry weight of the ingredients, dissolving an emulsifying agent in oil, mixing together and homogenizing the two solutions at 60°C to obtain an emulsion, and thereafter spray-drying the emulsion.
  • Chewing gum was prepared by admixing the carbohydrates with the mixture as cooled to 50°C, followed by addition of the flavoring at 40°C, molding and standing for cooling.
  • Table 32 Sweet chocolate Control Example Bitter chocolate 30.0 30.0 Sugar 55.0 - Dextrin (Example 1) - 54.7 Aspartame - 0.3 cacao butter 15.0 15.0 Dietary fiber 0.0 20.8 Dietary fiber/100 g 0.0 20.8 Caloric val.1(KCal/100 g ) 479 358 Caloric val.2(KCal/100 g ) 479 326
  • Example 38 Sweet jelly of beans Control Example Bean paste 42.0 42.0 Agar-agar 0.8 0.8 Water 7.2 7.2 Sugar 50.0 - Dextrin (Example 3) - 49.7 Stevioside - 0.3 Dietary fiber 3.02 18.8 Dietary fiber/40 g 1.21 7.51 Caloric val.1(KCal/100 g ) 257 165 Caloric val.2(KCal/100 g ) 257 137
  • indigestible dextrin was uniformly kneaded with wheat flour and further kneaded therewith while adding water in small portions to prepare spaghetti.
  • Table 41 The ingredients of Table 41 were fully kneaded together to obtain dough, which was then fermented and baked to prepare loaves of bread.
  • Table 41 White bread Control
  • crust dough was prepared by full kneading and repeated folding.
  • the inner ingredient was boiled down until it became half-deformed.
  • the dough and inner ingredient were molded and then baked to prepare an apple pie.
  • corn cream soup was prepared by boiling corn in water until no unboiled portion remained, then adding the other ingredients and boiling down the mixture.
  • Table 48 Corn cream soup Control Example Milk 19.8 19.8 Sweet corn 18.4 18.4 Butter 2.3 2.3 Wheat flour 2.0 2.0 Salt 1.0 1.0 Seasonings 0.2 0.2 Spices 0.2 0.2 Water 56.1 48.1 Dextrin (Example 4) - 8.0 Dietary fiber 0.45 2.05 Dietary fiber/200 g 0.90 4.10
  • Non-oil dressing was prepared according to the recipe of Table 51 by mixing liquid ingredients together and thereafter dissolving powdery ingredients in the mixture.
  • Table 51 Non-oil dressing Control Example Vinegar 33.0 33.0 Sugar 2.0 2.0 Salt 0.5 0.5 Soy-sauce 8.4 8.4 Seasoning (liquid) 26.3 26.3 Corn sirup solid 29.8 - Dextrin (Example 1) - 29.8 Dietary fiber 0 11.3 Dietary fiber/20 g 0 2.26 Caloric val.1(KCal/100 g ) 154 89 Caloric val.2(KCal/100 g ) 154 72
  • Embodister #30 listed in Table 52 is a lipophilic modified starch (product of Matsutani Chemical Industry Co., Ltd.).
  • Peanut butter was prepared according to the recipe of Table 54 by crushing raw peanut, pulverizing the peanut with an attritor and admixing other ingredients therewith.
  • Table 54 Peanut butter Control Example Peanut 60.0 40.0 Palm oil 40.0 26.0 Dextrin (Example 1) - 33.9 Peanut flavor - 0.1 Dietary fiber 5.20 16.4 Dietary fiber/20 g 1.04 3.27 Caloric val.1(KCal/100 g ) 705 520 Caloric val.2(KCal/100 g ) 705 500
  • White sauce was prepared according to the recipe of Table 57 by pan-frying soft wheat flour in butter, then mixing other ingredients therewith and boiling down the mixture until the mixture became thickened.
  • Meat sauce was prepared according to the recipe of Table 58 by pan-frying minced pork, onions and carrots in fat, pan-frying these ingredients again with addition of wheat flour, admixing other ingredients with the mixture and boiling down the resulting mixture until the mixture became thickened.
  • Corned beef was prepared from beef as held in a salt pickling solution for 5 days and boiled at 115°C for 90 minutes for the removal of water and fat. According to the recipe shown in Table 60, the other material was admixed with the beef to prepare a uniform mixture, which was then filled into a film bag, sterilized at 75°C for 60 minutes and thereafter refrigerated.
  • onions and beef were minced and mixed with all the other ingredients, and the mixture was uniformly kneaded and molded.
  • the molded piece was griddled on iron plate at 180°C over each side for 30 seconds, then boiled at 100°C for 10 minutes, cooled and thereafter frozen to obtain a frozen hamburger.
  • Hamburger putty was prepared according to the recipe of Table 62 by crushing the ingredients into a mixture, filling the mixture into a film bag having a diameter of 8 cm , thereafter freezing the mixture at -30°C and cutting the mixture into slices, 8 mm in thickness, by a slicer.
  • Table 62 Hamburger putty Control Example Beef 45.0 45.0 Poke 27.5 27.5 Fat (cow) 12.5 12.5 Onion 10.0 10.0 Spices 0.5 0.5 Salt 1.0 1.0 Sugar 1.0 1.0 Egg (whole) 2.5 2.5 Dextrin (Example 1) - 10.0 Dietary fiber 0.45 4.25 Dietary fiber/60 g 0.27 2.32
  • Liver paste was prepared according to the recipe of Table 63 by boiling liver, beef and belly at 100°C for 5 seconds, then crushing these ingredients, mixing them with the other ingredients, boiling the mixture at 80°C with full stirring and refrigerating the mixture.
  • the dough ingredients listed in Table 64 were fully kneaded together, then fermented at 40°C for 30 minutes in a heat-insulated device and cut into pieces of suitable size, which were spread out with a needle rod.
  • the ingredients for a pizza sauce were thoroughly mixed together and used after standing for at least 1 hour.
  • the sauce was applied to pizza crust followed by baking in an oven at about 230°C for 12 minutes to prepare pizza.
  • An omelet was prepared according to the recipe of Table 65 by dissolving indigestible dextrin in milk, admixing the solution with eggs along with the other ingredients and pan-frying the mixture in salad oil.
  • Table 65 Omlett Control Example Egg (whole) 90.0 90.0 Milk 30.0 20.0 Salt 1.0 1.0 Pepper 0.2 0.2 Salad oil 3.0 3.0 Butter 4.0 4.0 Dextrin (Example 4) - 10.0 Dietary fiber 0.15 2.13
  • a steamed Chinese dumpling stuffed with minced pork and frozen was prepared according to the recipe of Table 67 by mincing the vegetables listed, mixing them with the other materials after removal of water to obtain an inner ingredient, and wrapping the ingredient with a covering, followed by steaming at 100°C for 5 minutes, then by cooling and thereafter by freezing.
  • a blackberry liquor was prepared according to the recipe of Table 69 by immersing blackberries in distilled spirits for 40 days, discarding the blackberries and then aging the spirits for 2 months.
  • Table 69 Black berry liquor Control Example Black berry 57.0 57.0 Sugar 34.2 15.0 Dextrin (Example 3) - 19.1 Aspartame - 0.1 White liquor(70 proof) 65.8 65.8 Dietary fiber 0 6.05 Dietary fiber/100 g 0 6.05
  • Dog food was prepared according to the recipe of Table 70.
  • Table 70 Dog food Control Example Corn 25.0 25.0 Wheat and wheat flour 24.0 24.0 Born and meat meal 16.3 16.3 Soy bean waste 14.4 14.4 Fish meal 4.8 4.8 Wheat germ 2.9 2.9 Yeast 2.9 2.9 Animal fat 3.8 3.8 Vitamins and minerals 5.9 5.9 Dextrin (Example 1) - 10.0 Dietary fiber 4.70 8.50
  • Cat food was prepared according to the recipe of Table 71.
  • Table 71 Cat food Control
  • a feed for pigs was prepared according to the recipe of Table 72.
  • Table 72 Pig feed Control Example Corn 75.0 75.0 Soy bean waste 11.0 11.0 Bran 3.0 3.0 Fish meal 9.0 9.0 Calcium tri-phosphate 0.7 0.7 Calcium carbonate 0.6 0.6 Salt 0.3 0.3 Vitamins 0.2 0.2 Minerals 0.2 0.2 Dextrin (Example 1) - 10.0 Dietary fiber 6.95 10.8
  • a feed for broilers in the initial stage was prepared according to the recipe of Table 73.
  • Table 73 Feed for broiler Control Example Corn 44.65 44.65 Milo 10.0 10.0 Soy bean waste 23.0 23.0 Fish meal 9.0 9.0 Gluten meal 3.0 3.0 Alfalfa meal 2.0 2.0 Corn distiller's dried solubles 1.0 1.0 Animal fat 5.1 5.1 Salt 0.25 0.25 Calcium carbonate 0.6 0.6 Calcium di-phosphate 0.8 0.8 Lysine 0.05 0.05 Methionine 0.18 0.18 Vitamins 0.1 0.1 Choline chloride 0.05 0.05 Minerals 0.1 0.1 Nicarbazin 0.05 0.05 Oxytetracycline 0.07 0.07 Dextrin (Example 1) - 10.0 Dietary fiber 7.54 11.3
  • a feed for laboratory rats was prepared according to the recipe of Table 74.
  • Table 74 Feed for laboratory rat Control
  • Example Wheat 12.4 12.4 Oat 18.6 18.6
  • Corn 10.3
  • Barley 34.1 34.1
  • Bran 3.1 3.1 Fish meal 6.3
  • Skimmed milk powder 1.0
  • Alfalfa 1.6
  • Molass 1.0
  • Vitamins and minerals 0.5
  • Others 11.1 11.1 Dextrin (Example 1) - 10.0 Dietary fiber 6.22 10.0

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Nutrition Science (AREA)
  • Molecular Biology (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Inorganic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Husbandry (AREA)
  • Botany (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Materials Engineering (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Alcoholic Beverages (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Non-Alcoholic Beverages (AREA)
EP92116722A 1991-09-30 1992-09-30 Alkoholisches Getränk enthaltend ein unverdauliches Dextrin Expired - Lifetime EP0535627B1 (de)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP28049991 1991-09-30
JP280499/91 1991-09-30
JP336314/91 1991-11-25
JP3336314A JPH05148301A (ja) 1991-09-30 1991-11-25 難消化デキストリン

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EP0535627A1 true EP0535627A1 (de) 1993-04-07
EP0535627B1 EP0535627B1 (de) 1999-06-02

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EP (1) EP0535627B1 (de)
AT (1) ATE180789T1 (de)
DE (1) DE69229317T2 (de)
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GB (1) GB2260139B (de)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0616776A2 (de) * 1993-03-24 1994-09-28 Matsutani Chemical Industries Co. Ltd. Geflügelfutter
EP0646325A1 (de) * 1993-08-24 1995-04-05 Matsutani Chemical Industries Co. Ltd. Tierfutter, welches Fettleibigkeit verhindert
CN1037444C (zh) * 1994-09-17 1998-02-18 华南理工大学 难消化糊精的制备方法
CN1089768C (zh) * 1994-02-16 2002-08-28 瑞典淀粉生产中心 能量制剂
WO2006041021A1 (ja) 2004-10-08 2006-04-20 Matsutani Chemical Industry Co. Ltd. 食後の血中における中性脂肪の上昇抑制剤及びそれを含有する食品
FR2987360A1 (fr) * 2012-02-28 2013-08-30 Roquette Freres Maltodextrines hyperbranchees hypo-glycemiantes
CN104561191A (zh) * 2014-12-30 2015-04-29 山东百龙创园生物科技有限公司 一种抗性糊精的制备方法
WO2018007697A1 (fr) 2016-07-08 2018-01-11 Roquette Freres Composition de polymère de glucose hydrogénée contenant des fibres alimentaires
CN111455002A (zh) * 2020-04-14 2020-07-28 曲阜贝斯迪生物医药有限公司 一种抗性糊精的制备方法
US11390691B2 (en) * 2017-05-26 2022-07-19 Kabushiki Kaisha Yakult Honsha Oligosaccharide powder and method for manufacturing same
CN115651951A (zh) * 2022-12-29 2023-01-31 保龄宝生物股份有限公司 一种酶法辅助制备抗性糊精的方法
FR3142653A1 (fr) 2022-12-05 2024-06-07 Roquette Freres Compositions de cacao aux proteines vegetales a texture amelioree

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368451A2 (de) * 1988-10-07 1990-05-16 Matsutani Chemical Industries Co. Ltd. Verfahren zur Herstellung von Dextrin enthaltenden faserigen Nahrungsprodukten
EP0444891A1 (de) * 1990-02-26 1991-09-04 Matsutani Chemical Industries Co. Ltd. Verwendung eines Pyrodextrinhydrolysates zur Herstellung einer Nahrungsmittelzusammensetzung zur Verbesserung der Serumlipidzusammensetzung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH082270B2 (ja) * 1990-09-19 1996-01-17 松谷化学工業株式会社 食物繊維含有デキストリンの製造法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368451A2 (de) * 1988-10-07 1990-05-16 Matsutani Chemical Industries Co. Ltd. Verfahren zur Herstellung von Dextrin enthaltenden faserigen Nahrungsprodukten
EP0444891A1 (de) * 1990-02-26 1991-09-04 Matsutani Chemical Industries Co. Ltd. Verwendung eines Pyrodextrinhydrolysates zur Herstellung einer Nahrungsmittelzusammensetzung zur Verbesserung der Serumlipidzusammensetzung

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0616776A2 (de) * 1993-03-24 1994-09-28 Matsutani Chemical Industries Co. Ltd. Geflügelfutter
EP0616776A3 (de) * 1993-03-24 1995-02-22 Matsutani Kagaku Kogyo Kk Geflügelfutter.
EP0646325A1 (de) * 1993-08-24 1995-04-05 Matsutani Chemical Industries Co. Ltd. Tierfutter, welches Fettleibigkeit verhindert
CN1089768C (zh) * 1994-02-16 2002-08-28 瑞典淀粉生产中心 能量制剂
CN1037444C (zh) * 1994-09-17 1998-02-18 华南理工大学 难消化糊精的制备方法
WO2006041021A1 (ja) 2004-10-08 2006-04-20 Matsutani Chemical Industry Co. Ltd. 食後の血中における中性脂肪の上昇抑制剤及びそれを含有する食品
EP1797887A1 (de) * 2004-10-08 2007-06-20 Matsutani Chemical Industry Co., Ltd. Arzneimittel zur verringerung der zunahme von neutralem fett im blut nach einer mahlzeit und dieses enthaltendes nahrungsmittel
EP1797887A4 (de) * 2004-10-08 2009-07-29 Matsutani Kagaku Kogyo Kk Arzneimittel zur verringerung der zunahme von neutralem fett im blut nach einer mahlzeit und dieses enthaltendes nahrungsmittel
FR2987360A1 (fr) * 2012-02-28 2013-08-30 Roquette Freres Maltodextrines hyperbranchees hypo-glycemiantes
WO2013128121A1 (fr) * 2012-02-28 2013-09-06 Roquette Freres Maltodextrines hyperbranchees hypo-glycemiantes
US9783619B2 (en) 2012-02-28 2017-10-10 Roquette Frères Hypoglycemic hyper-branched maltodextrins
CN104561191A (zh) * 2014-12-30 2015-04-29 山东百龙创园生物科技有限公司 一种抗性糊精的制备方法
CN104561191B (zh) * 2014-12-30 2017-08-18 山东百龙创园生物科技股份有限公司 一种抗性糊精的制备方法
WO2018007697A1 (fr) 2016-07-08 2018-01-11 Roquette Freres Composition de polymère de glucose hydrogénée contenant des fibres alimentaires
US11390691B2 (en) * 2017-05-26 2022-07-19 Kabushiki Kaisha Yakult Honsha Oligosaccharide powder and method for manufacturing same
CN111455002A (zh) * 2020-04-14 2020-07-28 曲阜贝斯迪生物医药有限公司 一种抗性糊精的制备方法
FR3142653A1 (fr) 2022-12-05 2024-06-07 Roquette Freres Compositions de cacao aux proteines vegetales a texture amelioree
WO2024120655A1 (fr) 2022-12-05 2024-06-13 Roquette Freres Compositions de cacao aux proteines vegetales a texture amelioree
CN115651951A (zh) * 2022-12-29 2023-01-31 保龄宝生物股份有限公司 一种酶法辅助制备抗性糊精的方法

Also Published As

Publication number Publication date
ATE180789T1 (de) 1999-06-15
DE69229317D1 (de) 1999-07-08
GB9220468D0 (en) 1992-11-11
GB2260139B (en) 1995-10-04
EP0535627B1 (de) 1999-06-02
ES2132102T3 (es) 1999-08-16
DE69229317T2 (de) 2000-03-02
GB2260139A (en) 1993-04-07

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